With the Trump Administration’s continued crackdowns on Cuba regulations and remittances, Christopher Cloonan examines historical attempts at détente.
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Buildings in Havana often crumble from years of neglect. Photo credit: Karen Vierbuchen

President Trump has a personal determination to reverse many foreign-policy deals struck by President Barack Obama, as well as a political calculus to defer Cuba policy to the political and emotional interests of Cuban-American South Florida voters represented by notoriously anti-Cuba hardliner Sen. Marco Rubio (R). But this isn’t the first time in the history of US-Cuban relations that the Cuban people are left hanging after attempts at normalization. President Jimmy Carter’s attempted détente with President Fidel Castro in the late 1970s was the most successful bid at normalizing relations between the United States and Cuba since diplomatic relations were broken in 1961.

Why does this keep going wrong?

During Carter’s opening with Cuba, many positive steps were taken in an effort to move relations forward. Interests Sections were opened in respective capitals, political prisoners were freed in Cuba, and travel restrictions for Americans visiting Cuba were lifted. Not only could Cuban Americans send money to their relatives on the island, but they could visit them in person for the first time in nearly twenty years. It was the moment of hope that many Cuban people had waited for decades to arrive. But it didn’t last. More than three decades later, it was time to try again.

“…two independent polls conducted showed the overwhelming majority of Cubans thought a better relationship was good for Cuba.”

William LeoGrande

In 2014 President Obama moved toward truly normal relations with Cuba for the first time since then. Interest Sections became embassies, prisoners were traded, and Americans flooded Cuba by the hundreds of thousands to see an island that had been a “forbidden fruit” travel destination for over a half-century. President Obama met with President Raúl Castro on multiple occasions, even traveling to Havana to speak to the Cuban people directly. The Rolling Stones played before a million people in Havana, and Major League Baseball made its first return to Cuba in nearly two decades. The enthusiasm was palpable.

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The Rolling Stones performs during a free concert in Havana, Cuba in March 2016. Tens of thousands of people gathered for the free concert held days after an historic visit to the island by US President Barack Obama. Photo credit: EPA/Alejandro Ernesto

But as with Carter’s détente attempt, the joy would be short-lived. The enthusiasm of potential normalization faded into the bitterness of what could have been. In each case, the brief détentes, in some ways, produced more damage in their immediate aftermath than perhaps what would have occurred without the temporary thaws. 

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Presidents Barack Obama and Raúl Castro at a baseball game in Havana, March 2016. Photo credit: Chip Somodevilla (Getty)

Carter’s détente led many island Cubans to believe that they had lost out by not emigrating to the United States as they watched their relatives arrive flashing the latest fashions, displaying their relative wealth, and telling of enormous (if often exaggerated) success stories in their new country, while Cuba was simultaneously suffering through an economic recession. “The result was there was a sense on the island that the streets in Miami were paved in gold,” said Dr. William LeoGrande, Professor of Government at American University and co-author of Back Channel to Cuba: The Hidden History of Negotiations between Washington and Havana, in an interview with Startup Cuba. After the Freedom Flights —evacuation flights twice daily from Havana to Miami— ended in 1973, “there was pent-up demand for migration that had had no outlet. Put all these factors together —migration demand, recession, the apparent success of Cuban-Americans— when Castro opened the door, tens of thousands took advantage.”

In each case, the brief détentes, in some ways, produced more damage in their immediate aftermath than perhaps what would have occurred without the temporary thaws.

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The Cuban government allowed a flood of refugees to leave the island in what became known as the Mariel Boatlift, in April 1980. Cuba’s official state newspaper Granma denounced them as “delinquents, lumpenproletarians, antisocial and parasitic elements” while denouncing Carter, as cited in Back Channel to Cuba, as “an ‘insolent person’ who had ‘reached the peak of shamelessness’ by expressing his sympathy for the ‘criminals’ at the embassy” following Carter’s remarks sympathizing with “the almost 10,000 freedom-loving Cubans…at the Peruvian Embassy.” 

The Mariel Boatlift brought some 124,800 Cuban exiles to the US in 1980, contributing to the increase of Cuban immigrants in the US from 439,000 in 1970 to 737,000 by 1990. It contributed to diminishing the prospects of normalization in the long-term, as those economic refugees were absorbed into a political environment that was extremely hostile to Fidel Castro’s Cuba. 

Carter lost to Ronald Reagan in 1980, and shortly after, Cuba was placed on the State Sponsor of Terror List.

The Carter Administration had also caught the ire of the Cuban government by slowly processing former political prisoners’ entry into the United States after fighting to have secured their release in Cuba. The Administration additionally failed to prosecute Cubans who had hijacked vessels to take them stateside, despite the Cuban prosecution of American airplane hijackers who had landed on the island. These hijackings and attempted hijackings can be variously attributed to a desire for political asylum, terrorism, extortion, and mental illness, among other issues, with disagreements over the handling of the issue contributing to the rift between the two governments.

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Former Presidents Jimmy Carter and Fidel Castro in 2002. (Reuters)

This breakdown in relations, in addition to a multitude of disagreements over Cuba’s foreign policy in Africa, led to a failure in the effort to normalize relations. To the dismay of the Gerald Ford Administration, which had been contemplating its own normalization effort, Cuba sent troops to Angola in November 1975 in response to a South African invasion aimed at overthrowing Angola’s newly independent and communist-leaning government. The Cuban troops would not depart completely until 1991. Cuba had also participated on the Ethiopian side of the 1977–78 Ogaden War against a Somali invasion, which upset the Carter Administration as it had agreed to not let the Angola issue stand in the way of normalization but would not tolerate an “aggressive foreign policy in sharp conflict with U.S. interests in the Third World.” 

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Carter lost to Ronald Reagan in 1980, and shortly after, Cuba was placed on the State Sponsor of Terror List. Travel restrictions lifted by Carter were re-imposed, the only commercial air link between Miami and Havana was closed down, and a détente-era fishing agreement was allowed to lapse. Secretary of State Alexander Haig threatened to “turn that…island into a parking lot,” as Cuba feared an American attack. Driven by a growing Cuban-American voting bloc as a result of the Mariel Boatlift, the administration launched Radio (and later TV) Marti, American taxpayer-funded anti-Cuba propaganda broadcasting networks, much to the chagrin of Fidel Castro, who promptly suspended migration agreements and disallowed Cuban-American travel to the island. The atmosphere of progress had been lost. 

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Cuban troops in Angola. Photo credit: Pascal Guyot (AFP)

President Reagan, waging the Cold War, was only interested in normalization with Cuba on American terms, oft-implying a threat of military action against his adversarial neighbors. Reagan, however, was able to strike various deals with Cuba including bilateral migration agreements and accords ending the conflict in Southern Africa. 

In this latest attempt, Presidents Raúl Castro and Barack Obama brought the hope that the half-century of tense relations between the American and Cuban governments would finally come to an end. There was a feeling of inevitability surrounding the eventual lifting of the embargo. However, this would come to a grinding halt following Hillary Clinton’s loss to Donald Trump in 2016.

Reports of mysterious alleged “sonic attacks” against American and Canadian diplomats, followed by the President Trump Cuba announcement that President Obama’s Cuba deal was “canceled,” dashed hopes of a continued thaw in relations. Gradually, additional sanctions were levied against Cuba, travel restrictions increased (including the elimination of the “People-to-People” travel category and cruises originating from the United States). Caps on remittances were severely limited.

Later in 2019, the Trump Cuba policy led to ended flights to all airports outside of Havana (before the termination of all flights to Cuba due to COVID-19). Marriott International, Inc., operator of the lone American-run hotel, Four Points Sheraton, will not see its license renewed and will cease operations in the country at the end of August. 

The Trump Administration has also turned hemispheric relations against Havana, as Brazil, Bolivia, and Ecuador stopped using Cuban medical services (although Brazil reversed its stance due to the pandemic). 

Even Major League Baseball couldn’t escape the negative turn in relations. A 2018 MLB deal with the Cuban government to directly employ Cuban citizens —opposed to the previous system mandating Cuban citizens to defect to third countries before signing, often subjecting them to human trafficking— was rejected by the Trump Administration. 

“I saw a lot of entrepreneurs’ businesses flourish during Obama, being able to improve the life quality of many Cubans, owners, workers, and their families. Nobody thought that Trump would have such aggressive and negative policies against Cuba.”

Mario Otero

Diplomatic silence out of Washington regarding the April 2020 shooting at the Cuban Embassy by a Cuban citizen living in the US, and threats to once again designate Cuba as a State Sponsor of Terrorism, are signs that the animosity between the two governments will, predictably, continue during this American election year.

The well-intended efforts of peace-minded and détente-seeking administrations have twice failed to result in a lasting thaw, once again leaving the Cuban people disappointed. Many Cubans invested time, energy, and precious scant financial resources into small businesses such as casas particulares and paladares, only to see them go belly up as tourism diminished under Trump’s new regulations and has now paused entirely as the island closes its doors to foreign tourists amid the pandemic. Once-thriving people now struggle to feed their families. The countless Cubans who decided to stay and make a life for themselves by catering to international tourism, rather than leaving to chase the American dream, have been left behind in a country deserted of both the tourists and hope brought about by the Obama-era thaw.

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Casa particular owner Mario Otero and his wife Yolexis Rodríguez Duque, in Havana.

“In business and life, there’s always a risk,” said Mario Otero, the 30-year-old owner of Mayito’s B&B in Central Havana. “I saw a lot of entrepreneurs’ businesses flourish during Obama, being able to improve the life quality of many Cubans, owners, workers, and their families. Nobody thought that Trump would have such aggressive and negative policies against Cuba.” He continued, “If Trump is re-elected, Cuban entrepreneurs will be in an even more complicated situation.”

For those who had decided to leave Cuba anyway, many found themselves stuck at the Mexico-US border once the so-called “wet-foot/dry-foot” policy was rescinded by the Obama Administration in January 2017. The Trump Administration’s subsequent Migrant Protection Protocols require many asylum seekers to remain in Mexico while the US processes their cases. For Cubans, as recently documented by Vice Media’s “Cuban Hostage Crisis” on Showtime, this has made them particularly vulnerable to kidnappings and death threats as there is a general perception that their families in the US are relatively wealthy and willing to pay a ransom.

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Cuban migrants at Ciudad Juarez, Mexico in March 2019. Photo credit: Alejandro Bringas (EFE)

For President Carter, foreign-policy disagreements among other roadblocks ultimately prevented further progress on normalization efforts, just as with President Ford before him. For President Obama, congressional control of the embargo laws prevented a more irreversible thaw. For both, the inability to secure four more years of Democratic control of the White House ultimately doomed the staying power of their détente efforts. 

To be clear, the efforts made by Carter and Obama Administrations in and of themselves were worthy and noble. They were courageous efforts to right a historical wrong and further American interests. It was the stoppage of that progress by the Reagan and Trump Administrations that caused the initially-positive efforts by their predecessors to instead become damaging in some respects, including the resulting Mariel Boatlift under Carter and the now-shuttered tourism businesses opened under Obama. Some positive effects remained, including the freeing of prisoners. For Obama, it was especially important to attempt a détente during the presidency of Raúl Castro while Fidel Castro was still alive. This allowed the next Cuban president to continue the legacy of the Revolution rather than necessitate crossing it to facilitate peace with the United States.

But in both cases, the Cuban people are left behind to pick up the pieces of their shattered dreams. These failures will make it all the more difficult for future administrations to convince the Cuban people that the next thaw will stick and that history won’t repeat itself for the third time in as many tries. They must serve as a lesson for future administrations to ensure that progress cannot be reversed again. For US administrations, Cuba cannot become a political football. These efforts must be attempted once more in an even more aggressive and permanent fashion so they are successful in the long-term.

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A man tends the counter in his store while tourists pass by. Photo credit: Karen Vierbuchen

The Obama-era détente showed people in both countries what can and should be possible between them across many areas of cooperation. Regarding a potential third détente attempt in light of the issues brought about by the historical starts and stops, Dr. LeoGrande said that, “On balance, a third opening would be positive. The return of American visitors would boost the economy and the private sector. That will help the standard of living. It will increase visits by Cuban-Americans and increase remittances. When relations are good, family ties are strengthened. We can never be sure that there won’t be some negative externality that we can’t anticipate right now. But two independent polls conducted showed the overwhelming majority of Cubans thought a better relationship was good for Cuba.”

Casa particular owner Mario Otero agreed, saying, “I think that many people have hope of reinitiating Obama’s steps. People just want to improve their lives, be able to cover their necessities and have appropriate and respectful relationships with the US. This would be an ideal way to achieve that objective.”


  • Back Channel to Cuba: The Hidden History of Negotiations between Washington and Havana by William LeoGrande and Peter Kornbluh (The University of North Carolina Press, 2014)
  • Christopher Cloonan interview with William LeoGrande, June 2020
  • Christopher Cloonan interview with Mario Otero, June 2020

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Christopher Cloonan is an expert speaker on US-Cuba relations, Cuban history, traveling to the island, and more. He holds a master’s degree in Cuban Studies from Burlington College, and he studied abroad at the University of Havana. He has spoken at universities and libraries across the United States as he believes a brighter future is possible between our countries and that the pathway is through engagement, mutual understanding, sovereignty, and respect. He strongly encourages readers on both sides to consider the viewpoint from 90 miles away. He is also a baseball fan and is hopeful that sports diplomacy can help to advance relations. Fun fact: Chris recently discovered colorblind glasses and, subsequently, what actual colors look like.


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  • Hi Christopher. I just saw and read the article, and I am beyond impressed by it. I learned so much from you. Your excellent writing skills made all the information easy to digest. Your passion for the Cuban people is palpable, and your article left me deeply saddened about how far they’ve been set back. I was not a fan of Reagan and Trump is a disgrace on just about every level.

    • Thank you so much Rona! So nice to hear from you and thank you for taking the time to read my work. It was wonderful when I got the chance to see Dean in Havana. Hopefully, we can have a safe reunion soon!

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